Hydrochloric Acid → 3-(4-Bromophenyl)oxetan-3-amine hydrochloride

HRID 1047040노트

반응식

HRID 1047040 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:12]S(C(C)(C)C)=O)[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.[ClH:19]>ClCCl.C(OCC)(=O)C.CCCCCC>[ClH:19].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH2:12])[CH2:9][O:10][CH2:11]2)=[CH:6][CH:7]=1

참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 67067894N-(3-(4-bromophenyl)oxetan-3-yl)-2-methylpropane-2-sulfinamide

생성물 1

HCID 566046653-(4-Bromophenyl)oxetan-3-amine hydrochloride

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-[3-(4-bromophenyl)oxetan-3-yl]-2-methylpropane-2-sulfinamide (284 mg) in dichloromethane (17 mL) was added a solution of hydrogen chloride in ethyl acetate (4 M, 427 μl) dropwise at room temperature. After being stirred at the same temperature for 30 min, the reaction mixture was diluted with hexane. Filtration gave 3-(4-bromophenyl)oxetan-3-amine hydrochloride. To a solution of 3-(4-bromophenyl)oxetan-3-amine hydrochloride in THF (10 mL) and saturated sodium bicarbonate aqueous solution (10 mL) was added a solution of di-tert-butyl dicarbonate (403 mg) in THF (10 mL) dropwise. After being stirred at room temperature for 48 h, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate aqueous solution then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (5-30% ethyl acetate in hexanes) gave the product (194 mg, 2 steps 69%). 1HNMR (CDCl3) 400 MHz δ: 7.53 (d, J=8.7 Hz, 2H), 7.42 (d, J=8.7 Hz, 2H), 5.29 (br s, 1H), 5.01-4.90 (m, 2H), 4.85-4.73 (m, 2H), 1.50-1.26 (m, 9H). LCMS: 328, 330 [M+H].

후처리

  1. filtrationFiltration

출처 및 근거

ORD 기록
ord-c558befcc38146e59da07d27963acaf3
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569331B2

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